Sean Penn’s Rollercoaster Romances Unveiled

By Taylor McAdams, Oct 31, 2017

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Charlize’s Confession

Sean Penn is known to have dated quite a few celebrities throughout his career, but not-so-surprisingly, not all of them have great things to say about him. Today, some of them have spoken out in the most unexpected way…

No One Saw It Coming

Sean Penn has had some high profile relationships with a few well known celebrities, including Madonna and Robin Wright. Yet, he is probably infamous for his romance with Charlize Theron. Today, Charlize, as well as his other past love, have something to say about the actor.

He Moves Fast

Despite being of a scrawny nature with physical features that are less associated with Hollywood heartthrobs, he still, somehow, managed to intertwine flawless famed women in his web. The man who captivated the hearts of many women has been linked with stunning women like swimsuit model Jessica White, for example, right after his divorce from wife Robin Wright in 2009.

“I Do”

Although he is known for being quite a thrill seeker when it comes to romance, Penn actually walked down the aisle and said “I do” not only once – but twice. While it may seem hard to lock down a man like Penn, who is of a wild, experimental nature, he did willingly decide to be monogamous and swear to remain faithful two times in his life. The first marriage was the relationship most remembered to this day, but not for the reasons you may think.

No Happy Ever After

Indeed, Oscar-winning Sean Penn’s first marriage was to singer, actress, and trend-setter – Madonna. The two met in February ’85 and tied the knot only 7 short months after that – on the same day as Madonna’s birthday. They were young and in love, and for a while, it seemed like this relationship was going to stick. But then the most shocking news hit the fan.

Young Love

Before Sean and Madonna were linked, Penn was highly invested in making a future work with the dazzling Elizabeth McGovern. Penn fell madly in love with his Racing With The Moon coworker, proposed – and McGovern was quick to say yes. Unfortunately, she changed her mind shortly after and called off the entire thing, claiming she was too young and inexperienced to be set on a path so well-paved. “Married Sean?” said McGovern in an interview, rolling her eyes, “I think I was the lucky one to do what I did.”

High Standards

In 1996, Sean thought he would step out of his usual dating actresses zone and mix it up a bit. Maybe that is why he was seen arms-linked with Australian supermodel Elle Macpherson at an Upper East Side restaurant in New York. According to the New York Post, Penn and Macpherson were seen getting cozy: “They kept going up to the bar, the only place you can smoke in [restaurant] Coco Pazza. They kissed between puffs, and acted like no one else was in the room.”

Brainy Beauty

In 2009, Penn was linked to beautiful and brainy Natalie Portman. The two were rumored to be dining at the Sunset Tower Hotel’s bar when things got a little hot and heavy – only to be interrupted by the press who were trying to get a glimpse of the action. Disappointingly, Portman announced on E! Online that: “The reports that we are romantically involved are completely untrue. I normally do not respond to rumors about my private life, however, this repeatedly fabricated story has forced me to do so.”

Pride And Prejudice

Despite the fact the two claimed the rumors about their alleged affair were far from true, that did not stop the critics from having their blunt opinions heard. “It’s simply outrageous,” said a dumbfounded Hollywood insider to Soup Blog writers. “The idea that Penn, at 48 years old, would be involved with a woman of 27? She’s far too old for a star of his age. It’s downright sickening.” They say no publicity is bad publicity, but this seems to be the case of a fabricated tale spun out of control.

Mrs. (W)right

House of Cards star, Robin Wright, started seeing Penn almost immediately after his divorce from the Queen of Pop – Madonna. Being on-again-off-again from the start might not have seemed so reassuring for the dynamic duo, but it seems Penn thought Wright was Mrs. Right since he placed a ring on her finger six years after kicking off their rocky relationship. Unlike his former promise to be there in sickness and in health, this marriage stuck and talented two even brought kids into the world together.

Family And Flaws

Their first child is Dylan Frances, a daughter. Two years later, Hopper Jack was born, who is their second child and first son. Was the wild man finally tamed? Had he found his match – a woman that would challenge him as well as keep up with him, understand him for who he is and love him despite his flaws? Sean certainly hoped his mind and heart finally found peace, but as fate would have it, turbulence was fast approaching and unavoidable.

It Was Difficult

“It was…difficult,” Wright has said, referencing her marriage to Penn. After the pair wed in ’96, their relationship spiraled downhill right up until 2009. They announced their separation and went back on their words several times throughout this time period, claiming to have reconciled over their differences and finding a mutual ground that would ultimately save their marriage. Eventually, it seemed the relationship went sour for the last time, and that is when Penn filed for legal separation. But then, something shifted, and in 2010, Wright filed for divorce.

Living In A Lie

“When you get divorced, all the truths that come out, you sit there and you go, ‘What was I doing believing that this person was invested in this way?’ Which is a fantastically strong humiliation in the best sense,” said Penn in an interview to Esquire magazine. Among the many profound realizations Penn had from his previous marriages, the most intense one was that he does not feel as though he was ever loved by any of his former partners.

Party Penn

Readjusting to a life on his own and the concept of being single, Penn started seeing other people. “I thought, ‘Wow, I can actually go on a date.’ And so I go out, and I strike out four nights in a row, drinking at a bar and ending up home, you know, drunk,” he explained. But this was not the life he wanted. Feeling lost and unsure of what he should do with his life, Penn started looking for answers elsewhere.

The Moment It All Changed

After the divorce, Penn had a lot of time on his hands. Among the many new changes he underwent in his life at the time, Penn also started becoming more active in politics and philanthropic work. “I said [to myself], ‘I could just go sit in the middle of the bed and watch TV at four in the afternoon, too. I don’t have anything.’ My daughter’s … doing her thing, my son’s with his mother. So I turned on the TV and there was this earthquake in Haiti.”

Looking For Answers

“He used to drink a lot, and that got him into trouble,” a source relator to the actor revealed. “These days, he channels his aggression toward politics and trying to institute change. Being involved with Haiti really humbled him, and he’s even managed to cultivate a friendship with Madonna.” In the process of becoming more involved, Penn even co-founded his own non-profit: the J/P Haitian Relief Organization. But being the romantic-at-heart he has always been, Penn was missing someone special in his life.

Something Was Missing

“There is no shame in saying that we all want to be loved by someone. As I look back over my life in romance, I don’t feel I’ve ever had that,” he tells Esquire magazine. “I have been the only one that was unaware of the fraud in a few of these circumstances blindly.” Those words may sound harsh, but this was Penn speaking from the heart. However, instead of grieving over what was never truly his, he decided to look forward and elsewhere for love.

Music To His Ears

During one of the many off periods Penn and Wright had, the two thought it might be best to attempt seeing other people. One of the women Penn allegedly dated was singer Jewel. The rumor of their whirlwind affair seemed to make sense when news spread about Penn being named the director of Jewel’s “You Were Meant For Me” music video. In her book titled Never Broken – Songs Are Only Half The Story, Jewel tells the story of how she fell in love with the actor.

Thought It Was A Prank

Jewel received a call from Penn after he spotted her being interviewed on Conan O’Brien’s talk show. “I was twenty or so, something like that, and my dad thought it was a prank caller and hung up on him several times,” she said to Access Hollywood, excited to share the content of her book. “He had to keep calling back.” As it turns out, there was a reason for his persistence – Penn wanted Jewel to write a song for his 1995 movie, The Crossing Guard.

Her Way In

“He wasn’t flirty right away, he was business,” said Jewel, but there was an obvious admiration in her tone of voice that pointed towards something that was more than strictly professional. Additionally, Jewel said Sean was very sharp and had a great ear, not to mention – “very sweet.” The singer said the actor believed in her when no one else did, which is why she felt as though he understood her more than others. He flew her to Paris and Italy and introduced her to other A-list celebrities.

Nobody Believed

“Sean was very sweet,” said Jewel. “And it was a time in my career when nobody believed in me … But he really believed in me, and having that really meant a lot.” Jewel and Sean did not have a lengthy relationship or one that they claimed changed their lives, but it seemed as though it was exactly what they both needed at that stage in their lives. He was able to find love and admiration while stuck in an emotionless relationship, and she was granted the attention she craved.

Industry Politics

2011 was an interesting year in the life of Sean Penn, especially since his name was often brought up when mentioning one of the most sizzling actresses in the industry – Scarlett Johansson. If the telling picture of Scarlett’s foot casually placed to rest on Penn at a restaurant was not enough to prove the two had an intense dynamic going on, then attending the White House Correspondents’ Dinner together should have. However, Penn apparently broke things off with Johansson, claiming he was not into anything serious.

Nothing Serious

Sean broke things off with Scarlett after five short months, claiming he “didn’t want anything serious,” as was told by a source to Us Weekly. The same source also revealed that Scarlett was desperate to rekindle the flame, notably at the Spike TV’s Guys Choice Awards in Los Angeles, where the former lovers were snapped together. “She pushed herself into his conversations,” the source told Us Weekly. “She sat down between him and Robert De Niro. Robert was like “What?” and made a face.'”

Take A Picture, It’ll Last Longer

And in an incomparably awkward telling, Scarlett was allegedly very desirous to get a picture taken with her former lover: “A photographer asked for a shot,” a witness said. “Before Sean could say no, she said yes.” Although it doesn’t sound likely that the two winded up so estranged, it did seem as though Sean was tempting to avoid Scarlett on the red carpet, considering the fact he snuck in the back door while the then 26-year-old Lost In Translation actress arrived in a stunning white Valentino dress.

Not What It Seemed

An actor takes upon himself many roles, and if done successfully and skillfully, he may convince fans and the audience that he is the character he portrays. For this reason, many people confuse the character played in a TV show or movie with who the person really is – which could explain why fans were shocked when hearing that Penn had several uncharacteristic outbursts in his life. When it became public that Sean Penn was accused of being violent with Madonna, fans were sent into a tizzy.

Locked Behind Bars

Penn was on a movie set when suddenly, out of nowhere, he attacked a photographer. Like any other person, Penn craved some privacy and peace and quiet in his life, but after being denied this request from a paparazzi photographer, Penn lost his cool. The justice system sentenced the actor to jail for 60 days, although he ended up serving only 33 days in total. Shortly after this incident, Madonna filed for divorce – but then withdrew her papers for an unknown reason.

What Really Happened?

Come January 1989, The People, a Sunday tabloid magazine printed and distributed in Britain, ran a headline claiming that Madonna was attacked. The article went on to elaborate on Madonna’s New Year’s Eve being spent in an E.R. after she was supposedly beaten by her husband at the time. The singer was allegedly also strapped to an armchair against her own will, although this seemed very unlikely behavior for poor Penn. According to Peter Kent, the man who wrote the report, law enforcement from Malibu confirmed this peripheral involvement.

The Final Straw

“She is said to have been ‘frothing at the mouth’ when horrified staff freed her at 1 am on New Year’s Day,” read the report. “Madonna was weeping. Her lip was bleeding, her spirit was crushed. She was marked and sore where he had cracked her across the face.” Penn’s publicist, according to Kent, “shrugged off the incident as part of a young couple’s normal ‘ups and downs.’” Although the truth turned out to be much different than what was published, this was the final straw.

Hidden Secrets

The singer filed for the divorce for the second time following the incident, but unlike the first time, she followed through with her request to end their marriage. Almost two decades after their divorce, Madonna released a statement about the turn of events and what truly ended their passionate marriage. The “Material Girl” singer explained that while she understands the need to know what goes on behind the scenes, there are some things they rather keep to themselves.

Truth Comes Out

“The 57-year-old pop star said reports that Penn had struck her in 1987 and that he had tied her up and beat her in 1989 were false,” read an entry posted by the Daily Mail. According to ET, Madonna explained that while she is aware of the allegations made, these statements are “completely outrageous, malicious, reckless, and false.” Thankfully, the two let bygones be bygones, which enabled Penn to move on with his life towards more promising relationships, like the one that came knocking in 2013.

Undeniable Attraction

Come December 2013, Penn began dating South African beauty and award-winning actress, Charlize Theron. After only 18 months of going steady, the golden couple announced there was a reason for their flaunted PDA and rumors of adopting a child together – they were engaged to be married. This was Penn’s fourth engagement, but the one he seemed most certain of. When he was asked if Theron was his girlfriend, Penn said “no, excuse me, Charlize is not my girlfriend. She’s the love of my life.”

Heartbreaking Separation

Charlize was quoted saying she too felt that way and that she’s incredibly lucky to have a man like him by her side. However, the relationship fizzled, and out of the blue Charlize admitted to needing “a breather.” For a while, it seemed fans would never know what happened between the two and why Theron pulled the plug, but then she released a statement, saying: “We were in a relationship and then it didn’t work anymore. And we both decided to separate. That’s it,” she said.

Unexpected Behavior

Madonna’s marriage to Penn may have been short-lived, but that does not necessarily go to show their young love died. In fact, a year ago exactly the two brought up the idea of tying the knot again. Actually, it was Madonna who brought up the concept of remarrying – but she decided to it in a way no one ever anticipated – not even Sean Penn himself. Madonna is known to be quite a quirky gal, but this was unexpected behavior even for her.

Whip Out Your Wallet

During Miami’s Art Basel charity gala, a charity Madonna feels very passionate about, the two took the stage, and the most bizarre offer was made. It was a Friday night, and the 59-year-old was not about to let anything stop her from collecting as much money as she could from the respectively large crowd of rich and famous that stood in front of her. This list included the biggest names in the industry, including Leonardo DiCaprio, Bethenny Frankel, and – coincidently enough – Penn himself.

Memory Lane

Madonna already walked as though she owned the stage with her bold presence, and took it upon herself as a personal mission to sell off her jewelry and art collections in addition to the most sought-after auctioned experience of the night – a week at DiCaprio’s Palm Spring house. Another profoundly desired item sold was a car, but not just any car: this particular custom automobile was inspired by Madonna. But then, the seemingly normal auction became a saucy cruise down memory lane.

Music, Art And Mischief

The evening, as Madonna promised several times, was “an evening of music, art, and mischief,” and one the worldly and talented singer had hoped would raise plenty of funds for her charity, Raising Malawi. Bethenny Frankel, a star that gained recognition after the Real Housewives of New York, captured a video in which the singer is seen bringing her ex-husband on stage in an attempt to raise the bids on one of her necklaces significantly. Little did she know how successful this stunt was about to become.

Intimate Moment

Looking fresher than ever, Madonna had a few costume changes throughout the gala. When she brought her former lover on stage, she wore a short, poofy mini skirt and attached corset in a color that flattered her sunstricken hair. Those who were hoping history was repeating right in front of their eyes were about to be dumbstruck even more. The auction quickly turned into a saucy gathering of the two, who were quick to rekindle in the other’s arms as though the past wasn’t entirely in the past.

Remarry Me?

Zeroing in on her prosperous ex-husband and talented actor, Madonna offered to walk down the aisle again with the same man she invited to join her on stage if he was willing to bid $150,000 on a necklace. Penn seemed slightly blind sighted, but was willing to play along with her rather spontaneous and highly uncommon proposal – all in the name of charity. The Oscar-winner thought quick on his feet and promptly agreed – but then the unexpected happened.

In Front Of Her Son

Suddenly, the bridal waltz started playing, and Sean Penn found himself receiving a steamy too close for comfort less than private dance – in front of everyone in sight. Madonna then asked Penn if this particular moment reminded him of anything. The singer’s young son, David, was also at the gala, and although only 11-years-old, he got to see Penn receiving the intimate lapdance, then handcuffing his mother as some twisted joke on marriage. Then, the heat was turned up even more.

Teasing The Past

Once handcuffed, Madonna whispered into her microphone amusingly, “The many moments that were our marriage,” clearly insinuating towards the time the two were young and in love and the media spiraled into a frenzy discussing the unlikely reason the two went their separate ways. Even those who attempted to ignore the intimate innuendo could not do so, particularly when Madonna made the reference towards the night the police became involved in their affair and consequently tainted Penn’s public image.

Still In Love

Just when everyone thought the stage could not get any steamier, the tension could have been cut with a knife the minute the international, record-breaking singer whispered: “I’m still in love with you.” Speechless Penn then turned to find pictures of the pair were projected on a screen behind them. The photos, which were taken by Herb Ritts, featured very young versions of Penn and Madonna during their 1985 wedding. The two seemed very much happy and in love.

With Friends Like These…

Numerous outlets have asserted that despite Madonna and Sean’s repeated claims, the two are more than close platonic friends. However, one cannot help but wonder that if such rumors were true, would the two of them really been okay with sharing such a private moment on stage with the biggest names in Hollywood in sight? At the end of their onstage reunion, Penn’s willing and generous donation was outbid by other wealthy folks who had their eyes (and hearts) set on Madonna’s jewels.

A Woman With A Cause

Penn was also said to have dated activist and supermodel Petra Nemcova while he was on a break from his now ex-wife Robin Wright back in 2008, but the speculation has not been confirmed. But this was not the first time Penn fell for a woman who had strong opinions and fought for what she perceived at right. After Penn parted from actress Scarlett Johansson, Penn moved on to date Shannon Costello, who is the former communications director of his J/P Haitian Relief Organization.

May He?

Sean Penn was rumored to have a new leading lady – Leila George D’Onofrio. Vincent D’Onofrio’s 24-year-old daughter was said to spend time with the renowned actor by E! News, who claimed the two have been spending plenty of time together. Leila herself posted an Instagram shot of her with Sean in a recording studio working on an upcoming audiobook in Malibu. Multi-talented Leila was also been said to have caught the acting bug, and could be seen alongside James Franco in the film Mother, May I Sleep With Danger.

Fake Group Setting

Us Weekly was told by a source that less than two weeks after splitting from his long-time fiance Charlize Theron, Penn, actress Minka Kelly and a mutual friend went out to dinner for Minka’s 35th birthday. The three attended Thomas Keller’s prestigious restaurant The French Laundry in Napa, California. “That was their first date, but it was a group setting,” said the insider, clearly in the know. “It was more of a ‘let’s see how this goes.'”

Inexplicable Scene

Penn and Robin’s daughter Dylan dated musician Jimmy Giannopoulos, but in May 2017, an inexplicable scene occurred. Apparently, Sean, Robin, and Jimmy were having a quiet dinner at a cafe in New York, but when they headed outside things took a turn for the worse. A passerby told Radar that “Sean had his cell phone in his hand and held it up to Jimmy’s face to show him the screen. A heated exchange followed, and Sean’s face got redder and redder as he confronted Jimmy with whatever was on the phone.”

Never To Be Revealed

Jimmy was seen with his hand covering his mouth in shock as Penn inexplicably exploded, but he wasn’t the only one who could not hide his emotions. Penn’s ex-wife Robin apparently “broke down in tears, and Sean comforted her with a hug,” said the source. “Eventually, all three calmed down, and someone met them on the sidewalk, carrying their luggage,” meaning that things ended in a calmer manner. However, despite the trio’s hug before departure, one can’t help but wonder what caused such a stir.

The Big Bang

Mexican actress Kate del Catillo, mostly known for her work on her lead role in the telenovela Muchachitas, traveled with Penn to Mexico in 2015. The actress, who has a reputation as a thrill-seeker in many circles, claims to have met with the international illegal substance lord Joaquin ‘El Chapo’ Guzman alongside Penn, and has recently released information regarding their less official relationship to the media after claiming Penn was trying to put a pin in her career.

It’s Just Business

Castillo claims Penn heard of her intention to pull a three-part Netflix documentary series titled The Day I Met El Chapo: The Kate del Castillo Story and decided to block her off her dream. The documentary is supposed to act as a mirror of the truth, said Castillo, which will enable her to tell “a fascinating story” of how she fell for the MysticRiver actor, despite having established the fact they were not romantically involved prior to anything physical happening.